Sulfolane → 2-Fluorobenzonitrile
Reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1S(Cl)(=O)=O)#[N:2].[F-:13].[K+].S1(CCCC1)(=O)=O>>[F:13][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]#[N:2]Participants
4
Procedure
20.15 grams(0.l mole) of the product prepared in Example 1 above, 12 grams(0.21 mole) spray-dried potassium fluoride, and 45 milliliters sulfolane were heated under nitrogen to 230°-248° C. for one hour. The product was distilled directly through a 5-inch(12.7 centimeters) vigreaux column to give 6.9 grams 2-fluorobenzonitrile having a boiling point of 91°-92° C. at 27 mm Hg. The infrared spectrum was identical with that of the published spectrum. Based on 2-cyanobenzenesulfonyl chloride, the per cent yield of 2-fluorobenzonitrile was 57. Based on saccharin, the overall yield was 52.
Workup
- distillationThe product was distilled directly through a 5-inch(12.7 centimeters) vigreaux column
Sources & evidence
- ORD record
- ord-be87c42575794f509f4b2935a67acbb2
- Source dataset
- uspto-grants-1992_01
- Patent number
- US05081275
Reaction notes
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